Download PDF
Synthesis 2008(11): 1805-1807  
DOI: 10.1055/s-2008-1032117
PSP
© Georg Thieme Verlag Stuttgart · New York

A One-Step, Safe Synthesis of 2,4-Dinitrostyrene and Related (Di)nitrodivinylbenzenes via Stille Coupling

Nathalie Eloy, Eric Pasquinet*, Eric Grech, Frank David-Quillot, Olivier Besnard, Didier Poullain
CEA Le Ripault, BP16, 37260 Monts, France
Fax: +33(2)47345142; e-Mail: eric.pasquinet@cea.fr;
Further Information

Publication History

Received 12 December 2007
Publication Date:
06 March 2008 (online)

    Permissions and Reprints All articles of this category

Abstract

A one-step synthesis of 2,4-dinitrostyrene is described. Based on a Stille coupling, the procedure is more amenable to scale-up than the existing methods that require longer reaction sequences and hazardous nitration processes. This easily polymerizable monomer was isolated using a continuous extraction method. The reaction was extended to the synthesis of two other related vinyl monomers including the previously unknown 1,3-dinitro-4,6-divinylbenzene.

Key words

Stille reaction - cross-coupling - polymers - nitro compounds - styrenes

    References

  • 1 Boileau J. In Materials Research Society Symposium Proceedings   Vol. 418:  Brill TB. Russell TP. Tao WC. Wardle RB. Materials Research Society; Pittsburgh: 1996.  p.91 
    Search in Google Scholar
  • 2a Barba NA. Nedelko MS. Shukla RK. Koordinats. Soedin. Perekhod. Elementov. Vopr. Khimii i Khim. Tekhnol., Kishinev  1983,  108 ; Chem. Abstr. 1983, 99, 158944
  • 2b Shukla RK. Ind. Polym. Radiat. Proc. Symp.  1979,  33 ; Chem. Abstr., 1981, 94, 103903
  • 3 Barba NA. Botnar MS. Pogrebnoi IL. Manole SF. Sint. Fiz.-Khimcheskoe Issled. Koord. Polim. Soedin.  1986,  118 ; Chem. Abstr. 1987, 107, 78281
  • 4 Barba NA. Botnar MS. Manole SF. Pogrebnoi IL. Izvestiya Vysshikh Uchebnykh Zavedenii, Khimiya i Khimicheskaya Tekhnologiya  1987,  30:  40 ; Chem. Abstr. 1988, 109, 73079
    Search in Google Scholar
  • 5 Sapozhnikov OY. Mezhnev VV. Dutov MD. Shevelev SA. Russ. Chem. Bull. Int. Ed.  2005,  54:  1048 
    CrossrefSearch in Google Scholar
  • 6 Barba NA. Shukla RK. J. Org. Chem. USSR  1977,  13 :  609 
    Search in Google Scholar
  • 7a Gandler JR. Yokohama T. J. Am. Chem. Soc.  1984,  106:  130 
    CrossrefSearch in Google Scholar
  • 7b Naruta Y. Ishihara N. Tani F. Maruyama K. Bull. Chem. Soc. Jpn.  1993,  66:  158 
    CrossrefSearch in Google Scholar
  • 8a Farina V. Krishnamurthy V. Scott WJ. Org. React.  1998,  50:  1 
    Search in Google Scholar
  • 8b Kosugi M. Fugami K. In Handbook of Organopalladium Chemistry for Organic Synthesis   Negishi E. Wiley; Hoboken: 2002.  p.263 
  • 9a Buynak JD. Ramana Doppalapudi V. Frotan M. Kumar R. Chambers A. Tetrahedron  2000,  56:  5709 
    Search in Google Scholar
  • 9b Kashin AN. Bumagina IG. Bumagin NA. Beletskaya IP. J. Org. Chem. USSR  1981,  17:  18 
    Search in Google Scholar
  • 10 Detert H. Sugiono E. J. Prakt. Chem.  1999,  341:  358 
    CrossrefSearch in Google Scholar